(a) Interpretation: The detailed mechanism for the given equation of cross aldol reaction using a weak base such as pyridine is to be drawn. Concept introduction: Like aldehyde or ketone , the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

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Answer 1

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 18, Problem 18.72P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the given equation of cross aldol reaction using a weak base such as pyridine is to be drawn.

Concept introduction:

Like aldehyde or ketone, the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

Interpretation Introduction

(b)

Interpretation:

Why a relatively weak base can be used in the given crossed aldol reaction of diethyl malonate it is to be explained.

Concept introduction:

Like aldehyde or ketone, the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

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The crossed aldol reaction shown here can be carried out using a weak base such as pyridine. (a) Draw the complete, detailed mechanism for this reaction. (b) Explain why a relatively weak base can be used. EtO OEt H EtO OEt H. Diethyl malonate

Shown here is a proposed synthesis of a thioester from an ester. (a) Draw the mechanism for this reaction. (b) Would this reaction be energetically favorable? Why or why not?

(a) Predict the product of the set of reactions shown here. (b) Draw the complete, detailed mechanism for the formation of the synthetic intermediate that is not shown.

Answer 2

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 18, Problem 18.72P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the given equation of cross aldol reaction using a weak base such as pyridine is to be drawn.

Concept introduction:

Like aldehyde or ketone, the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

Interpretation Introduction

(b)

Interpretation:

Why a relatively weak base can be used in the given crossed aldol reaction of diethyl malonate it is to be explained.

Concept introduction:

Like aldehyde or ketone, the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 18, Problem 18.72P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the given equation of cross aldol reaction using a weak base such as pyridine is to be drawn.

Concept introduction:

Like aldehyde or ketone, the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

Interpretation Introduction

(b)

Interpretation:

Why a relatively weak base can be used in the given crossed aldol reaction of diethyl malonate it is to be explained.

Concept introduction:

Like aldehyde or ketone, the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 18, Problem 18.72P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the given equation of cross aldol reaction using a weak base such as pyridine is to be drawn.

Concept introduction:

Like aldehyde or ketone, the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

Interpretation Introduction

(b)

Interpretation:

Why a relatively weak base can be used in the given crossed aldol reaction of diethyl malonate it is to be explained.

Concept introduction:

Like aldehyde or ketone, the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

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Answer 5

Chapter 18, Problem 18.72P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the given equation of cross aldol reaction using a weak base such as pyridine is to be drawn.

Concept introduction:

Like aldehyde or ketone, the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

Interpretation Introduction

(b)

Interpretation:

Why a relatively weak base can be used in the given crossed aldol reaction of diethyl malonate it is to be explained.

Concept introduction:

Like aldehyde or ketone, the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

Answer 6

Chapter 18, Problem 18.72P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the given equation of cross aldol reaction using a weak base such as pyridine is to be drawn.

Concept introduction:

Like aldehyde or ketone, the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

Answer 7

Chapter 18, Problem 18.72P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the given equation of cross aldol reaction using a weak base such as pyridine is to be drawn.

Concept introduction:

Like aldehyde or ketone, the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

Answer 8

Interpretation Introduction

(b)

Interpretation:

Why a relatively weak base can be used in the given crossed aldol reaction of diethyl malonate it is to be explained.

Concept introduction:

Like aldehyde or ketone, the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

Answer 9

Interpretation Introduction

(b)

Interpretation:

Why a relatively weak base can be used in the given crossed aldol reaction of diethyl malonate it is to be explained.

Concept introduction:

Like aldehyde or ketone, the diethyl malonate having α hydrogen can be converted to a good nucleophile by reacting it with a weak base. The diethyl malonate, in the presence of a base, undergoes deprotonation at the α carbon (the carbon between two carbonyl groups) and forms stabilized carbanion, which can be resonance stabilized by both carbonyl groups. The carbanion undergoes nucleophilic addition reaction with polar π bonds like aldehyde or ketone, similar to crossed aldol reaction.

Answer 10

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Answer 13

Ch. 18 - Prob. 18.1P Ch. 18 - Prob. 18.2P Ch. 18 - Prob. 18.3P Ch. 18 - Prob. 18.4P Ch. 18 - Prob. 18.5P Ch. 18 - Prob. 18.6P Ch. 18 - Prob. 18.7P Ch. 18 - Prob. 18.8P Ch. 18 - Prob. 18.9P Ch. 18 - Prob. 18.10P

Solution Summary: The author explains the mechanism of cross aldol reaction using a relatively weak base such as pyridine.

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